HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl 2',5'-difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate → 1-(2',5'-Difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl 2',5'-difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-carboxylate | HCID 57705744 | — |
| Reactant | HCID 178418306 | HCID 178418306 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 1-(2',5'-Difluoro-4-(hydroxymethyl)-1,1'-biphenyl-2-yl)-2,2-dimethyl-1-propanone | HCID 57706182 | 85% |
Reaction Steps
To a stirred solution of 83.27C (0.485 g, 2 mmol) in THF (17 mL) at −78° C. was added tert butyl lithium (3 mL, 5 mmol, 1.7 M). The reaction was then stirred for 1.5 hours and then quenched with a saturated solution of ammonium chloride and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-40% EtOAc in hexanes) to yield 83.27D as a colorless oil (0.450 g, 85% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030354B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-339a2c087c7e44e988ce056b5c564250 |
| Source note | uspto-grants-2011_10 |